Synthesis and antimicrobial activity of halogenated derivatives of 2-benzylidene-1-(1,2,4-triazol-1-ylmethyl)-cyclohexanols

Abstract

Human and animal mycotoxins generated by Fusarium fungi have been studied by many researchers for a long time [!]. One of the most dangerous toxin producers is Fusarium graminearum, which is responsible for alimentary toxicosis; it was known earlier as "bread made of contaminated grain" [2]. In addition to the fact that the control of this phytopathogenic compound presents great difficulty in agrocenosis, it is practically impossible to prevent grain disease in the case of fusariose. There are compounds among derivatives of IH1,2,4-triazole that are of interest not only as systemic fungicides [3] but also for treatment of mycosis [4]. We continued the search for antifusarial nitrogen-containing compounds, which could be used both as means for plant protection and chemotherapeutic agents. This paper presents the results of the synthesis and investigation of antimicrobial properties of a number of triazolylcyclohexanois (XII) containing the 4-halogenobenzylidene group at C-2 and hydrogen atoms, monomethyl, or dimethyl groups at C-6. The scheme describes the synthesis of the target triazolylcyclohexanols XII. When developing this scheme, we proceeded from the known fact of triazolylcycloalkane formation by opening of oxiranes (XI) formed from the corresponding enones (VII) with 1,2,4-triazole [5]. The choice of the pathways for the synthesis of required enones VII is a key problem in the preparation of triazolylcyclohexanols XIi. Synthesis of 6-monomethylenones (Vllb) was carried out by condensation of 2-methylcyclohexanone (Ib) with haIobenzaldehydes under the action of an aqueous solution of KOH in ethanol [6]. 6,6-Dimethylenones (Vllc) were obtained by alkylation of 6-monomethylenones Vllb with methyl iodide [7]. Attempts to obtain benzylidenecyclohexanones (Vlla) without substituents at C-6 by condensation of cyclohexanone (la) with 4halobenzaldehydes under alkaline

DOI: 10.1007/BF02331857

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Cite this paper

@article{Krimer2006SynthesisAA, title={Synthesis and antimicrobial activity of halogenated derivatives of 2-benzylidene-1-(1,2,4-triazol-1-ylmethyl)-cyclohexanols}, author={M. Z. Krimer and V. P. Tashchi and Yu. B. Kal'yan and F. Z. Makaev and Yu. G. Putsykin and O. Yu. Molchanov}, journal={Pharmaceutical Chemistry Journal}, year={2006}, volume={29}, pages={764-769} }